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Toluene → HCID 39359537、化合物

HRID 1626750
ノート
印刷プレビュー

反応式

HRID 1626750 の反応式
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[O:18][CH2:19][C:20]([O:22]CC)=[O:21].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C.CO>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:15]1[CH:27]=[CH:26][CH:25]=[C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])[CH:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 5197439Ethyl 2-(3-bromophenoxy)acetate

生成物 1

HCID 39359537HCID 39359537、化合物収率 58.2%

試薬・触媒・溶媒 4

HCID 178418397
HCID 178418397、化合物
触媒
HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Under an Ar atmosphere, 12 mL of toluene, 3 mL of methanol, and 3 mL of 2M aqueous sodium carbonate solution were added to 500 mg (1.93 mmol) of ethyl (3-bromophenoxy)acetate and 352 mg (2.32 mmol) of (2-methoxyphenyl)boronic acid, and the mixture was degassed. Further, 112 mg (0.097 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and the mixture was heated under stirring at 80° C. for 6 hours. After the mixture was cooled to room temperature, ethyl acetate and water were added thereto to separate the mixture. The water layer was separated, and filtration was performed. Thereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate was performed. The organic layer was washed with saturated saline and dried over anhydride magnesium sulfate, followed by filtration and condensation, thereby giving 290 mg of [(2′-methoxybiphenyl-3-yl)oxy]acetic acid (yield: 58%).

後処理

  1. customthe mixture was degassed
  2. temperaturethe mixture was heated
  3. temperatureAfter the mixture was cooled to room temperature
  4. customto separate the mixture
  5. customThe water layer was separated
  6. filtrationfiltration
  7. extractionThereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate
  8. washThe organic layer was washed with saturated saline
  9. dry with materialdried over anhydride magnesium sulfate
  10. filtrationfollowed by filtration and condensation

出典と根拠

ORDレコード
ord-b8613a952c0d4ab0a39a0d825367a162
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785473B2

反応ノート

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